In the ’90s, there were some seriously despised villains roaming around. They weren’t out to conquer the world or obliterate everything in their path, but man, were they obnoxious. Picture those messy characters in movies who didn’t quite deserve our support, yet we found ourselves secretly rooting for them because their rivals were such despicable scoundrels. Take Billy Madison, for instance. He may not be your typical hero, but when he squares off against the slimy VP Eric Gordon, it’s hard not to cheer him on.
Movies have their fair share of truly wicked villains who can never be redeemed. We’re talking about the likes of the Joker or Buffalo Bill, who have committed heinous acts and show zero remorse. However, there’s another breed of characters who aren’t exactly evil, but boy, are they hard to like. Sometimes, these characters are even more detested than the actual murderers. Perhaps it’s because they remind us of those individuals we’ve encountered in our own lives. We might never cross paths with a villain like Thanos, but we’ve all come across that pompous person at a fancy club who thinks they’re superior to everyone else. And let’s face it, those encounters are never pleasant.
1. Dennis Nedry
Dennis Nedry may not have been the main antagonist in Jurassic Park, but his incompetence and selfishness easily made him the most despised character in the film. His sole focus on his bank account led him to accept a bribe to steal dinosaur embryos from the very park that employed him. In order to carry out this act, Nedry foolishly disabled the park’s security system, oblivious to the fact that it was the only thing keeping him and the other humans safe from the dinosaurs. While Nedry wasn’t inherently evil, his demise at the hands of the Dilophosaurus didn’t elicit much sympathy from the viewers.
2. Caledon Hockley
In every Romeo and Juliet-esque cross-class relationship, there’s usually a rich guy who’s a bit of a jerk, engaged to the woman at the beginning of the movie. Eventually, she realizes she actually loves the poor man who may not have much to offer her. And despite her family’s disapproval, she decides to leave the jerky rich guy for him. This is exactly what happened with Caledon Hockley in Titanic.
When Caledon Hockley first met Jack, he didn’t hold back and called him “filth.” Now, it’s understandable that Caledon would be angry to see another man getting too close to his fiancée, but labeling him as “filth” seemed a bit extreme. Then, to top it off, Caledon tried to give Jack a measly $20 as a thank you for saving his own fiancée.
Sure, Caledon may have had more to offer Rose, and his actions weren’t necessarily evil, but he was enough of a jerk that no one is exactly rushing to buy a Team Cal shirt.
3. Phillip Stuckey
Pretty Woman is all about Edward Lewis, a businessman who unexpectedly finds himself smitten with Vivian, a lady of the evening. Unfortunately, not everyone in Edward’s circle is open-minded about Vivian’s line of work. Enter Edward’s lawyer, Phillip Stuckey, who takes the prize for being the ultimate jerk in the movie.
From start to finish, Stuckey treats Vivian horribly, going so far as to make unwelcome advances. His disdain for her profession is crystal clear, and it’s safe to say he views her as less than human. In the grand scheme of film history, Stuckey solidifies his position as one of the biggest jerks ever depicted.
4. Shooter McGavin
In the movie Happy Gilmore, Adam Sandler played a relatable character who didn’t quite fit into the snobbish world of professional golf. One of the main snobbish characters in the film was Shooter McGavin, a professional golfer. Now, Shooter may not have been trying to take over the world or have someone eliminated, but he certainly was a jerk. He acted as an antagonist to Happy Gilmore on the golf course, but their rivalry ran much deeper than that.
Shooter displayed his rudeness by treating everyone around him poorly. There was a scene where he demanded a businesswoman who was pitching to him to stop talking and bring him a Pepsi. Later on, when Happy’s grandma faced financial difficulties and her house was put up for auction, Shooter intentionally bought it just to spite Happy and force him to quit golf. Shooter’s behavior was so appalling that, even after losing the golf tournament, he tried to steal the golden jacket and ended up being chased by a crowd of angry fans.
Overall, Shooter McGavin was not a likable character. His actions throughout the film showcased his arrogance and mean-spirited nature.
5. Sheriff of Nottingham
When the King of England went off to fight in a war, the Sheriff of Nottingham stepped in to govern the people in his absence. Unfortunately, the Sheriff’s rule was far from fair, and his terrible attitude only made things worse.
To give you an idea of his behavior, there was a moment when the Sheriff actually said, “Cancel the kitchen scraps for lepers and orphans. No more merciful beheadings. And call off Christmas.”
6. Carl Bruner
Sam Wheat, a banker, was tragically murdered while investigating a case of banking trickery. Surprisingly, his best friend, Carl, seemed to step in and support Sam’s girlfriend, while also taking it upon himself to investigate the murder. However, it was later revealed that Carl was actually involved in the crime alongside his co-conspirator, Willie.
Now, let’s be clear, killing and stealing are undeniably wicked acts. However, the disdain towards Carl goes beyond what his crimes warrant, primarily because of his despicable character. It is truly appalling that he would eliminate his own friend and put his girlfriend’s life at risk, all for a measly amount of money. As if that wasn’t enough, he even went on to physically assault two women in the movie before resorting to pulling out a gun on them.
7. Gaston
The Beast in Beauty and the Beast wasn’t exactly a pleasant character. His own jerkiness led to the curse on his castle, and he went on to imprison Belle and her father. On the other hand, all Gaston did was attempt to rid his town of the terrifying beast who was kidnapping people.
However, despite Gaston’s noble intentions, his arrogant and jerkish behavior made it impossible for the audience to root for him. He was such a jerk that he couldn’t even show a hint of kindness when a room full of people sang praises of his greatness.
8. Eric Gordon
Billy Madison, the son of a wealthy businessman, was often seen as immature and disruptive. Despite lacking the qualifications, he was set to inherit his father’s company solely due to nepotism. On the other hand, Eric Gordon, a diligent and hardworking Vice President at the company, seemed like a deserving candidate to take over. However, his unpleasant demeanor made the audience root for Billy instead.
During the academic decathlon, a competition that Billy had to win in order to prove his capability to run the company, Eric’s true colors were revealed. In a surprising turn of events, he lost the competition because he couldn’t answer a question about business ethics. It was astonishing that he couldn’t even define the term “business ethics.” This incident caused him to lose control and react irrationally, pulling out a gun on Billy Madison.
9. Pat Healy
Pat Healy, a private investigator, was hired by a guy named Ted to uncover the current whereabouts and activities of his childhood crush, Mary. Little did he know that this assignment would take an unexpected turn. Pat managed to track down Mary in Miami, but instead of just gathering information, he found himself falling head over heels for her. Unfortunately, Pat was not the only one vying for Mary’s affection, as there were many other love-struck individuals in her life.
In his desperate attempts to win over Mary, Pat resorted to lies, stalking, and whatever else he believed would make her fall for him. However, his deceitful tactics eventually came to light. Even in his misguided pursuit of impressing Mary, Pat displayed a complete lack of understanding on how to be a decent person. For instance, he falsely claimed to work with special needs children, using a derogatory term to refer to them. He even went as far as sharing disturbing details about how he supposedly kept some of them in cages and others on leashes.
Overall, Pat’s actions were not only unethical but also revealed his complete disconnect from basic human decency. His misguided obsession with Mary led him down a path of deception and manipulation, ultimately jeopardizing any chance of a genuine connection with her.
10. Meredith Blake
In “The Parent Trap,” Annie and Hallie, who are twins separated from each other, come together to try and reconcile their parents. Throughout the movie, they face opposition from their father’s girlfriend, Meredith Blake, who is primarily interested in his wealth. While there is technically nothing morally wrong with marrying someone for their money, Blake’s terrible personality makes her appear just as villainous as characters like Thanos or Emperor Palpatine.
Blake’s intentions to make money were so evident that even the girls’ nanny openly expresses doubt about her genuine feelings for their father. It is clear that Blake has numerous ulterior motives, including her interest in his financial resources located in the Napa Valley bank.
11. Wilson Croft
Wilson Croft not only shamelessly profited from stolen ideas belonging to his former friend, the brilliant scientist Philip Brainard, but he also had the audacity to set his sights on Brainard’s wife. From the very beginning, Croft ridiculed Brainard’s invention of Flubber, but as soon as he realized its potential for financial gain, he conspired with other individuals to exploit it for personal profit.
Croft’s despicable actions extended beyond mere theft and greed. He took pleasure in toying with Brainard’s emotions, openly flirting with his wife and even making a tasteless bet. He callously wagered that he would either take her out for a fancy dinner or whisk her away on a mountain trip, further adding insult to injury.
However, justice was eventually served when Croft faced the consequences of his actions. In a delightful turn of events, he was later knocked out by none other than Flubber itself, leaving us all with a gratifying sense of comeuppance.
